
House holiday rentals in Charlemont
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Top-rated house rentals in Charlemont
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Popular amenities for house rentals in Charlemont
House rentals with a pool

The 1770 House
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

Berkshire Mountain home views, pool, Queechy Lake
We had a fantastic stay here - it is a wonderful place that truly does look and "feel" just like the AirBnB profile. The AC unit wasn't functional unexpectedly but we had nice weather and it wasn't a big deal. Even with that hiccup we happily give this place a 5/5 stars. We plan on coming back, and imagine it will be one of our favorite places upstate to visit

The Brick House on Washington Street
We had such a wonderful stay at this historic home! Ruth was a great host and was easy to communicate with, even when I needed to message her late at night. The rooms were great and it was in a perfect location. We are looking forward to booking here again next year.

Family/Dog Friendly Mountain Home w/ Amenities
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.

4bed, 2bath @ Chimney Hill w/Hot Tub & EV Charger
Lovely home. Hopefully I can stay here next year.

Stylish Chimney Hill Home - Close to Mt. Snow!
No complaints. This is a beautiful home that had everything we needed for our weekend ski trip with 4 adults and 1 toddler. Very clean, cozy and a great location close to Mt. Snow. We really enjoyed our stay, thank you!

Stylish Rural Sanctuary with POOL!
We had a wonderful stay at this beautiful property! The location is close to plenty to do and great dining but also feels very private. The home is absolutely beautiful as pictured. The pool was a real treat to have and half of the pool is a shallow end which was a bonus for us traveling with a child. The beds are very comfortable which is always a huge plus when traveling. The hosts were responsive with any questions that came up. We would happily stay again!
Weekly house rentals

J&J’s Retreat
What a retreat! This was a lovely stay in a beautiful home which was well decorated and every little detail was thoughtful. Our family enjoyed our stay - thank you!

Above the Oaks - Modern Luxury near Berkshire East
This is such a beautiful airbnb that my group of mom friends decided to come back for our 2nd annual mom's getaway weekend! There's more than enough space for us to relax and chat and we loved having access to the hot tub too. The kitchen and bathrooms are pristine and have everything we need. I highly recommend this place!!

The Camp
Great value for the price. Four guests plus my pup stayed at Marie’s place. All the comforts of home. Everything for meal prep was provided. Bathroom was stocked with plenty of towels and washcloths. Wifi worked well. Beautiful sound of the river right in the back yard was a bonus. Was a perfect base camp for us to look at possible land to buy in the future. Will definitely be back to continue our search.

Rustic 1850s Barn. Updated and funky.
We had a fantastic time and the house was lovely! WE would 100% stay with Yvonne again. Thank you for a wonderful time.

Charming Brookside Artisan Home
We have had the pleasure of staying here before. It is perfect for our needs. Conveniently located. Quiet. Comfortable beds and a great back porch for enjoying coffee in the morning. It is very clean and well-maintained.

1810 Brook-Side Mill/EV 2 Charge
Comfortable, cozy, clean and peaceful house for our family of three. We each had a floor with a full bathroom, and great amenities throughout. We particularly loved being between great skiing at Berkshire East and the beautiful town of Shelburne Falls.

2.5mi from the lake! Fire pit, arcade, yard games!
My 2nd time staying here. Always amazing. Check out Sprague and Sons Sugar House. Home baked breads, Maple Products, Cookies absolutely delicious. Even Maple Ice Cream and home baked Chocolate Chip Cookie with Maple Ice Cream sandwiches. The home is absolutely gorgeous and has Everything you need or want. Great stay. Eric is so helpful and welcoming. Very responsive to messages any time you need him. Thanks for an Incredible Experience. We hope to be back again soon.

Magical, Rural Getaway in the Berkshires
This is a truly peaceful and comfortable home in a beautiful spot. The house is well appointed and everything is clearly explained. The nights are dark and super quiet.
Private house rentals

Cambridge Hill Farmhouse - Sauna - Swimming Pond
This was such a lovely country escape for us tired city kids. The pond was a beautiful backdrop for reading and drawing. We brought our binoculars and walked across to Dan B road, spotting gorgeous birds multiple times a day. Our host, Danielle, was extremely responsive and friendly. A fuse blew our second night there, and Danielle had an electrician out to fix it the next day so we could sleep with AC that night. One warning: if you're tall, there are some very low ceilings and doorways. My partner is 6'2 and hit his head repeatedly on the bathrooms' vaulted ceilings and the kitchen doorway. The house would be great for a big group, or a family with kids -- the playroom is delightful and the big, fun kitchen makes you want to fill with your friends and eat and talk for hours. We're very grateful for our quiet getaway there!

Bridge of flowers cottage
Our family converged on Shelburne Falls from several faraway places for a nearby college graduation. We rented 5 nights in order to make it a family reunion. This lovely home turned out to be the perfect setting, as it has a large amount of common living space, in several adjacent rooms, so that we could be all together or in smaller groups. We enjoyed meals in the large kitchen, sitting by the fire, short walks to good restaurants and handy grocery stores. We sat on the porch enjoying the garden. The area is quiet and safe. The trains coming through at the bottom of the garden were entertaining, but didn't wake people up because the trains go very slowly through a sunken section and don't honk nearby. The town is delightful, and plenty of hiking and things to do (Clark Art Museum!) nearby. As longtime AirBnBers, what we appreciated most is that this is really a family home, with an attentive host and a helpful neighbor/manager. In other words, AirBnb at its best!

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.
This is only my second time using an Airbnb. The house is just gorgeous, everyone was comfortable, our family was impressed, all amenities were available. We saw two deer, bluebirds and had an aerial show from hang gliders. The view is really spectacular including all views from all windows. I had trouble with the lock but my son was familiar. I'm just old and inexperienced. All in all, highly recommend this property.

Magical Retreat Cottage - Waterfalls everywhere
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Beaver's Bend Lakefront Retreat &~16 Mi to Slopes!
Beautiful home in an even more beautiful location. This is the second time we stayed at Brian’s home and we’re excited to make this trip again!

Comfortable Entire Farmhouse close to North Adams
We had a lovely time at Maura’s house! Maura was friendly and responsive and clearly loves to share this beautiful area with guests. The house was spacious and well kept. (I would note for those who might mind that there were some family photos, magnets, etc. up, but that didn’t bother us at all!) The house is about 10 minutes from Mass MOCA and less than 20 minutes to Williams College.

New & Cozy~Near MoCa~Deck~River
This is a delightful place! It's very near town but off the road so it's quiet. The house is larger than I expected and extremely tranquil and restorative. The sound of the creek just outside the porch is incredible! And Marin was a lovely and responsive host. Highly recommend.

Colorful Urban Cabin Steps from Mass MoCA
Eli's home is in a great location; easily walkable to MassMoca and downtown. It's small but cute and has everything one needs to cook, rest, etc. There are a couple of things to be mindful of... - The upstairs bedrooms get quite hot in the warm weather, and the ACs are very loud, as is the fan. I highly recommend bringing earplugs; we only had one pair, and my husband didn't sleep well during the hot night (we both slept well the other nights!). This is not the first time we've experienced this at an Airbnb, and it would be super nice if hosts provided quiet ACs for their rentals. Eli is responsible, so I'm sure he'll figure out an alternative. The bed was very comfortable! - There are a lot of steep stairs (inside and out), which normally isn't an issue, but we were traveling with our heavy e-bikes and had to carry them up and down the stairs, and that kept us from going for several spontaneous bike rides. Overall, we enjoyed our stay at Eli's and would recommend his home.
Quick stats about house rentals in Charlemont
Total rentals
10 properties
Nightly prices starting at
$64 SGD before taxes and fees
Total number of reviews
430 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Taconic State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Stratton Mountain Resort
- Norman Rockwell Museum
- The Shattuck Golf Club
- Magic Mountain Ski Resort
- Beartown State Forest
- Bright Nights at Forest Park
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Pineridge Cross Country Ski Area